Embark on your next adventure. Join our team as an Island Caretaker!

Posted: Oct 09, 2026

Island Caretaker

Bayberry Administrative Services LLC

East Hampton, New York

Wages/Pay
$2,000.00 / week
Experience Level
Some experience required
Job Start Date
Nov 01, 2026

Our small team brings diverse backgrounds and experiences to the job and members are excited to learn new skills. Our culture thrives on people who love nature, appreciate history, respect their colleagues, and are not afraid of working hard in the outdoors.

You will work primarily outdoors in all seasons. Maintaining the island means a lot of physical and manual work, but we encourage you to take the time to stop and soak in the views, serenity, and wildlife.

You can expect to live and work on this incredible island, so no commuting or rent expenses.  We hire for a 4-month term and work will change as the seasons change. We are actively hiring for a Caretaker position for a November start date. 11/1 is noted as the start date, but we are flexible. 

How to Apply

Contact Info

Bayberry Administrative Services LLC

We are a family dedicated to preserving and stewarding a ~3,000-acre island off the coast of Long Island, New York. The island is rich in historical significance and has been in the family for hundreds of years. Most importantly, it is an extraordinary wildlife sanctuary. Our goal is to continue to preserve and maintain the island for many future generations.

Location
New York
Season
Winter
Staff size
3-5
Housing
Whether included in the compensation package or provided at a cost, housing is provided for staff.
Housing details
Each caretaker is given their own room with conjoining bathroom access.
Family housing available
No
Pet friendly
No
Meals
Provided
Cell phone service
Yes, most carriers
Internet access
Good
About CoolWorks

Since 1995, CoolWorks has connected adventure-seekers with job opportunities in amazing places—from national parks to ski resorts, summer camps to dude ranches. We help people trade screen time for real time—meaningful experiences that spark connection and growth. Your next great adventure is waiting. More About CoolWorks

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